


A chip off the block

by DeadLegato After Dark (deadlegato)



Category: Hazbin Hotel (Web Series)
Genre: F/M, Mildly Dubious Consent, Sir Pentious Has Two Penises (Hazbin Hotel), cherrisnake
Language: English
Status: Completed
Published: 2020-12-03
Updated: 2020-12-03
Packaged: 2021-03-10 05:27:38
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,231
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27859822
Author URL: https://archiveofourown.org/users/deadlegato/pseuds/DeadLegato%20After%20Dark
Summary: Cherrisnake smut. Cherri bets the snake three blocks of contested turf that he isn't man enough to handle her.
Relationships: Cherri Bomb/Sir Pentious (Hazbin Hotel)
Comments: 5
Kudos: 47





	A chip off the block

It was another day in Pentagram city, and other turf battle between a cyclops, a snake, and a scattering of rotten eggs. Angel wasn’t available to help Cherri that day, but as Pentious hadn’t fully rebuilt his armory yet since their last big battle, she could more than handle him on her own.

“Come out from behind that wall and fight like a man, you crawling snake!” she called, ducking down quickly as a laser blast went over her head. It felt more like a game of laser tag than a life-or-death battle for real estate supremacy. Not that demons could die other than to angelic weapon, mind you, but having to regenerate hurt like a bitch.

“You can’t insult me by calling me a snake and then complain that I act like a snake!” Pentious shouted back, ducking down behind his own wall as another bomb flew overhead. “Why don’t you come out from behind _your_ wall?”

“Because I don’t fight like a man, I fight like a woman!” she answered, and he had to roll to avoid another shot she’d taken at him. “What’s the point of having two dicks if you’re too shit to use either of them?”

“Who told you…” he ducked another bomb and quickly moved from behind one fallen beam to another. He was annoyingly fast and slippery for his size. “Who told you that?? And excuse me, MISSY, I can very much use both of my dicks!”

“Yeah, right! I bet even going full force with both of ‘em you could get me off once!”

“I’m sorry, but you’re just going to have to remain jealous of my sexual prowess, as I am…” he had to roll again, avoiding another of her blasts as pieces of concrete and brick fell around his head. Flat on his belly, he aimed to return fire. “Leagues above you!”

“Ha, you missed me!” she said as his shot went wild.

“Did I?” he asked, and a huge piece of brick from above her came down and slammed her on the head.

“Ow, that’s dirty, you slug!” That stung more than she had thought it would. She was going to have a lump from that.

“Oh, suddenly you care about playing fair??” he asked with a huge Cheshire grin, clearly enjoying that he’d managed to land a hit on her.

“Whatever. I’d be willing to bet these entire three blocks that you couldn’t make me climax once before you emptied both your cannons.” Speaking of canons, it was time to pull out some bigger guns.

“Oh, would you really?” he asked in annoyance, avoiding the bricks that were falling as she was now also aiming over his head. He took cover underneath a burnt-out car while she was distracted knocking out a few overly confident eggs that thought they could take her on. “Maybe I would take you up on that offer, if I wanted to contact syphilis.” He had better put that taunting snake tongue back in his mouth if he wanted to keep it.

“I do not have any STDs, although I imagine you do, ancient snake-boy. You’re older than antibiotics, aren’t you?”

“Excuse me, but I’m actually discerning when it comes to where I put my _two dicks_. You probably take anything that will fit!”

“Is that what you’re afraid of? That your dicks are too small for me?”

“WHY ARE WE HAVING THIS CONVERSATION!?” he asked in frustration.

“Because it’s distracting you,” she said with a grin, as she’d used his flustered distraction to get on top of the car he was hiding under and aim her RPG launcher straight down through it. He just barely had enough time to realize what she was up to and skitter from underneath the car, but that didn’t leave him with enough time to get to cover again before she was on top of him, stomping down on his tail.

“What part of your body am I going to blow off first?” she asked, her launcher directly in his face.

Looking around frantically, he lunged forward and grabbed her hand. “I accept your bet!” he said suddenly, grabbing and shaking her hand.

“You accept my… aaah!” she cried in shock as their hands lit up, sealing the bargain. “I… I… I wasn’t serious!!”

“The rules of Hell don’t have a loophole for ‘I wasn’t serious!’” he mocked back at her, using her temporary distraction at her hand glowing to pull his tail out from under her, throwing her down on her butt. “You could always just say I’ve won the bet and hand over this territory to me. No fornication necessary.”

“I should put a hole in your chest right now,” she answered, weapon still tight in her hands.

“It wouldn’t matter if you did. If you don’t agree to the terms of your own bet, you still forfeit!” he jeered, grinning. He was obviously pleased with himself, based on his facial expression and the position of his hood.

Bastard snake thinks he’s won, she thought. “Fine. You better bring your a-game, snake, cuz these blocks are as good as mine.”

His shit-eating grin and his hood fell. It was clear he’d expected her to give up, not to agree to it. He wasn’t anticipating having to do anything. “Agreed. Then… uh… your place… or mine?” It was clear his brain was spinning, trying to think of what he was supposed to say next.

“I don’t want to go to your place. You’ve probably got arsenic-laced wallpaper.”

“I like that green, and it is not like it can poison me anymore! I don’t want to go to your place. I bet it is a roach-infested heap.”

“Ugh, fine, you stubborn worm. We’ll get a hotel.”

“I don’t want to be seen going into a hotel with you!” Was it just her imagination, or had the thought slightly caused him to flush? Could snakes even blush?

“Then you admit, you forfeit?” she asked, looking down the barrel of her weapon at him.

“… Fine, a hotel,” he huffed, crossing his arms in annoyance.

She finally pulled her launcher away from his head. “You’re paying.”

“Why am I paying?!” he shrieked.

“Because you’re the man, obviously.”

“Well that’s quite… sexist,” the snake pouted.

“I thought you were from the pre-feminist era.”

“That doesn’t mean I still oppose equal rights for women.”

“When it comes to paying for a hotel room.”

“Well… yes!” he said, exasperated, making an open-palm hand gesture to show his frustration.

.

Several days later…

.

He clearly didn’t think I’d go through with it, Cherri reasoned. He thought he was getting an easy win. I’m not letting Edgelord get away with that. Besides, she was willing to bet he’d chicken out at the last minute anyway. She didn’t care how many dicks he has; she was certain he didn’t have the balls to with them.

Or at least, he’d _better_ chicken out at the last moment, she thought as she waited in the hotel lobby, pouting and leaning up against the wall. I bet he won’t even show. I bet he’ll tuck his tail between his… well, okay, he doesn’t have legs to tuck a tail between, but still. Wasn’t having a streak of yellow down the back a sign of cowardice? And he had a huge one.

“Oh, Miss Bomb,” she heard an obnoxiously shrill, loud voice call her in a sing song tone. She flinched.

“Do you have to be so loud? I thought you were the one who didn’t want to be seen with me,” she snapped. She looked around to make sure she didn’t know anyone else in the lobby.

“If you’re so embarrassed, you could still forfeit,” he said in that same singing tone.

“If you’re trying to out-shame me, snake boy, you should know I have no shame.”

“Fine, if that is how you want to be,” he said, oddly punctuating between the words. “Shall we check in? I brought you flowers, by the way,” he said, giving her what was obviously a five-dollar special from the supermarket on the corner. “You can’t say I’m not a gentleman.”

.

“So…” the snake said, not making eye contact with her. He was sitting in one of the nasty overstuffed chairs while she sat on the bed. He did not want to know what all those stains on it were from. “How do you want to do this?”

“Rather than sitting around talking about it, let’s just get this over with.” She suddenly stood up and whipped off her top, throwing it on his head.

“Hey! Ugh, don’t you wear deodorant?” he asked, pulling her shirt off his face.

“I bet you can’t even get as far as taking the bra off, snake boy,” she crowed.

He gave her a very tired look. As she looked at him confidently, she suddenly felt something touching her back, and had to grab onto her bra as the back clasp came open. She turned around to see his tail behind her. “With… with your tail?” Okay, maybe that was impressive. She faced him with a cold expression and let her bra drop, flopping backwards onto the bed. “Next challenge: Bet you don’t know how to take shoes off, Mr. No Legs!” she said, waving a foot at him.

“Are you trying to disgust me into stopping?” he asked, removing his hat and placing it on top of the television. “I am not the type of man to have a foot fetish, I am sorry to inform you,” he said. She was right on one aspect, though. He had a significantly harder time getting her long boot off than he did getting her bra off, which amused her. “How… how do you get into these pants?!” he demanded, huffing slightly. “Did you glue them on?!”

“Hey, I gave you at least one break today. I’m not wearing any underwear.”

“… Lovely,” he said dully. He ended up toppling completely backwards when he finally got her leggings off, as he had to pull very hard to make the final pass over her ankles.

“Now you gotta get naked, snake boy.”

“Mmm, when I’m good and ready,” he answered. He seemed… hesitant. “Are you… are you really okay with this? I don’t want to… have non-consensual sexual relations with anyone, even someone as loathsome as you.”

“Maybe you should have thought of that before you shook my hand! Look, I’m getting cold, so if you’re going to do this, just DO it.”

From the look he was giving her, she half expected him to turn around and leave. She wasn’t ready for him to grab her ankles and pull her to the edge of the bed. She was _completely_ unprepared for him to lower himself down, placing his head between her legs. “Wait, what are yoooooouuuuuu…”

“Please, don’t tell me you’ve never had cunnilingus before,” he said between flicks of his tongue against her clit and her labia. She had seen how snake tongues flicked before, she’d just never imagined what that would feel like with a snake between her legs, holding the entrance to her slit open with a very light pressure from his fingers.

“I said dicks… not… tongues…” The sensation would touch, press slightly, and then immediately move away. It was strangely pleasurable, more than she would have thought. Shit, was there any chance in all the nine circles he knew what he was doing? She would have pegged him for a hopeless hundred-year-old virgin.

“You never said no tongues either. It is quite rude to enter an unprepared partner.”

She knew that she was getting wet, but that was to be expected. It was a basic biological response. It wasn’t like he was any better than a cheap vibrator. It wasn’t like… Ooooooh, shit. What was he doing? How did he know the swirly trick? Who told him that? How could…? Her back was arching slightly on its own, wanting to push his tongue further into where she wanted it. Just the tip of her hood wasn’t enough. No, no, she was _not_ getting off on this. Okay, so snake read a few men’s magazines. It wasn’t like…

He changed his pressure, going from just flicking at her to full out pressing her button, rubbing against her like a textured vibrator. Every sense in her said to grab onto his hood hair and start pulling him where she wanted him to go, but she wasn’t going to make it easy for him. She dug her fingers into the sheets. Think of completely unsexy things, she thought. Then again, what could be un-sexier than an old man, and there was one currently going to town on her. She felt something pressing against her, pushing inside her, questing the space of her vagina. Is that his tiny dick? No, it can’t be. He’s not in the right position. He was exploring her with his fingers.

Her swollen clit tingled under his tongue. A cry escaped her, and she heard him let out a smirking chuckle in response. There was no way she was losing to an ancient, Victorian-era snake. Think of cold showers. Think of… of… but it felt so good. It felt like electricity passing from her hips to her breasts. Shit. Shit. If this kept up, she was going to cum before he even got a dick out. She bit her lower lip, hard, trying to feel the pain from the sharp tips of his fingers instead of the pleasure from the way they were exploring her.

Suddenly, he stopped. Her first thought was ‘why did you stop???’ but instead, she panted out “What… what’s wrong? Out of energy already?”

“Missy, please. I’m just about to get this show on the road,” he answered her with a grin, removing his bow tie and then his coat. She hadn’t realized it before, but he didn’t wear a shirt under his jacket. The yellow scales went all the way up his chest, surrounding the one large eye sitting between his collarbones.

It was then that she’d realized why he hadn’t previously undressed. He’d had her naked and vulnerable to him that entire time while he remained armored, clothed. The snake was smarter than she’d given him credit for.

“What, what the hell are those?!” she asked when the main act finally arrived on scene, emerging from a slit set deep within his scales.

“You said you knew I had two dicks,” he responded in a sickeningly false-innocent voice.

“I didn’t know they were covered in spikes and shit! You’re not… you’re not going to penetrate me with that, really?!”

“They’re not sharp. I’m not a cat. Of course, you could always surrender, or I could finish you off without even needing to use…”

“Put up or shut up,” she said angrily. “Stick it in.”

The snake leaned over her, his belly scales cold up against her chest. “Very well.”

She grunted as he pushed himself inside her. He was bigger than she’d anticipated. “What’s the… what’s the matter…” she groaned. “That the fastest you can go, old man?”

“I can go faster if you’d like, my dear,” he answered, and she regretted taunting him. He was hitting her in just the right spot, the feel of his spikes rubbing up against her insides unlike anything she’d experienced before. She’d messed around with rubbery spikes on dildos before, but this was different. It was like someone gently brushing her from the inside out, causing her to shudder.

She was not prepared for him to turn that tongue on her breasts. He could wrap it around her nipples, one at a time, pinching them. The pressure on her rough nipples beneath his mouth increased, causing them to tent. As she grew more and more aroused, her skin tightened, everything wanting to stand up. She kept trying to think about anything other than the fucking. Between the thrusts between her legs and the mouthing on her breasts, she couldn’t stop her thoughts. Shit. I’m going to lose. I’m going to lose. Well, if… if I’m going to lose… I might as well make this worth three blocks, she thought.

Her legs came up and wrapped around his hips, moving with him as he thrust inside her. Letting him so, so much deeper. She dug her fingers into his back, clawing at his scales, wanting to break skin as she screamed. She didn’t even care anymore, she just screamed. He was panting heavily, obviously not used to that much physical activity.

She was caught off guard when he suddenly came inside her, fully, flushing her with his sperm. The surprise broke through the last remaining mental guard she had against him, and she came. Her insides tightening and releasing, pulsing around him, continuing to quiver long after the main act was over. He waited until all motion from her delicate insides and her rocking hips stopped before pulling out, dripping with a mixture of their fluids.

“You… you technically came first,” she panted.

“You… said I had until I used both dicks…” he answered back, trying to recover his lost breath.

“That’s right. If I’m giving up three blocks, I deserve both dicks.”

“Can you take both? I might break you,” he asked smugly. “You seemed quite frightened at the prospect of taking even one of them.”

“Try me, snake bastard.”

They repositioned entirely on the bed so that he could put his full weight on top of her, thrusting deeply into her, licking at and flicking his tongue around her breasts. They were both huffing and panting, lungs crying out for them to stop but the electric feeling in their pelvis telling them both to go, go, to keep going. To keep pushing harder and harder, in and out. She was pulling on his hair with both hands, finding it weird to the touch because his hair was attached to the skin of his hood and not free flowing like she had expected.

He kept striking against the perfect, raised spot inside her. Shit, shit, how had he found it so quickly? Did he have… did he have eyes on his dick?! Well, no time to worry about that. She decided to let go, and came before him this time, the feeling of her vagina closing around him causing him to climax shortly after her, finally letting out a scream of pure, raw lust. She wasn’t a sound she had expected him to be able to make.

“Fu… fuck… I should… I should have only bet you two blocks. That was a fuck worth two blocks, but I’m not sure it was worth three blocks,” she chided him as he collapsed onto his side, breathing hard. She was sweating, and he would have been if he were able to. “Fuuuuuck, I didn’t know you had it in you, literally.”

“Age and treachery will overcome youth and skill every time,” he responded with what little breath he had. She doubted he had enough air left in him to say more.

They both lay there quietly, staring at the ceiling. “… Leave immediately or sleep it off?” she asked.

“I’m going to sleep it off. I’m paying for this room, after all. You can leave if you want,” he answered, rolling over.

“Fuck, if I’m losing that much territory, I’m taking everything I can get,” she answered.


End file.
